Digital Masters, such as Starbucks, that leverage digital technologies effectively, differentiate themselves from their peers by consciously striving to build a close relationship between IT and the business. However, Digital Masters are exceptions. The IT-business relationship in most organizations is often a fractious relationship rather than a marriage of equals. Business teams often find the IT department’s high costs and long implementation timelines unacceptable. In addition, IT leaders are often faulted for not speaking the language of business. Leading CIOs take this disconnect head on and try and fix it. Our research shows that leading CIOs take three key actions to align the IT department with the needs of the business: 1. redesign the IT department to unlock digital innovation; 2. create strong digital platforms; 3. rationalize IT Infrastructure to fund digital initiatives. We explore each of these actions in this research paper.